(-)-(S)-4-(tert-butyl-diphenyl-silanyloxy)-3-methyl-thiobutyric acid S-ethyl ester

Base Information

• Chemical Name: (-)-(S)-4-(tert-butyl-diphenyl-silanyloxy)-3-methyl-thiobutyric acid S-ethyl ester
• CAS No.: 948859-72-1
• Molecular Formula: C₂₃H₃₂O₂SSi
• Molecular Weight: 400.657
• Mol file: 948859-72-1.mol

Synonyms:(-)-(S)-4-(tert-butyl-diphenyl-silanyloxy)-3-methyl-thiobutyric acid S-ethyl ester

Chemical Property of (-)-(S)-4-(tert-butyl-diphenyl-silanyloxy)-3-methyl-thiobutyric acid S-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(S)-4-(tert-butyl-diphenyl-silanyloxy)-3-methyl-thiobutyric acid S-ethyl ester

There total 5 articles about (-)-(S)-4-(tert-butyl-diphenyl-silanyloxy)-3-methyl-thiobutyric acid S-ethyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

C22H28O2SSi + methylmagnesium bromide (75-16-1) → (-)-(S)-4-(tert-butyl-diphenyl-silanyloxy)-3-methyl-thiobutyric acid S-ethyl ester (948859-72-1)

Guidance literature:

methylmagnesium bromide; With C₃₆H₄₄FeP₂*Cu⁽¹⁺⁾*Br^(1-); In diethyl ether; tert-butyl methyl ether; at -78 ℃; for 0.5h; Schlenk technique; Inert atmosphere;

C₂₂H₂₈O₂SSi; In diethyl ether; tert-butyl methyl ether; at -78 ℃; for 17h; Schlenk technique; Inert atmosphere;

DOI:10.1002/anie.202105384

Reference yield: 96.0%

(E)-4-(tert-butyl-diphenyl-silanyloxy)-but-2-enethioic acid S-ethyl ester (917590-73-9) + methylmagnesium bromide (75-16-1) → (-)-(S)-4-(tert-butyl-diphenyl-silanyloxy)-3-methyl-thiobutyric acid S-ethyl ester (948859-72-1)

Guidance literature:

methylmagnesium bromide; With (R,S(Fe))-Josiphos/CuBr; In t-BuOMe; diethyl ether; at -78 ℃; for 0.333333h; Inert atmosphere;

(E)-4-(tert-butyl-diphenyl-silanyloxy)-but-2-enethioic acid S-ethyl ester; In t-BuOMe; diethyl ether; at -75 ℃; for 18h; Inert atmosphere;

With methanol; In t-BuOMe; diethyl ether; at -75 - 20 ℃; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1002/chem.201001284

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → (-)-(S)-4-(tert-butyl-diphenyl-silanyloxy)-3-methyl-thiobutyric acid S-ethyl ester (948859-72-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 79 percent / imidazole / tetrahydrofuran / 24 h / 20 °C

2.1: iodoxybenzoic acid / ethyl acetate / 24 h / Heating

3.1: 80 percent / CH₂Cl₂ / 24 h / Heating

4.1: (R,S_p)-Josiphos CuBr complex / diethyl ether; various solvent(s) / 0.17 h / -75 °C

4.2: 95 percent / diethyl ether; various solvent(s) / 17 h / -75 °C

With 1H-imidazole; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; (R,S_p)-Josiphos CuBr complex; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; 3.1: Wittig reaction;

DOI:10.1021/ol071078o

upstream raw materials:

(E)-4-(tert-butyl-diphenyl-silanyloxy)-but-2-enethioic acid S-ethyl ester

methylmagnesium bromide

(tert-butyldiphenylsilanyloxy)acetaldehyde

2-[(tert-butyldiphenylsilyl)oxy]ethanol

Downstream raw materials:

(S)-4-(tert-butyldiphenylsilyloxy)-3-methylbutanal

(-)-(E)-(S)-6-(tert-butyl-diphenyl-silanyloxy)-5-methyl-hex-2-enethioic acid S-ethyl ester